Synthesis of 4-hydroxybenzyl alcohol

Preparation of 4-hydroxybenzyl alcohol

Alternative Names: 4-hydroxybenzyl alcohol; 4-(Hydroxymethyl)phenol; 623-05-2; P-Hydroxybenzyl alcohol; P-Methylolphenol; 4-Methylolphenol;

30 g of phenol are dissolved in 150 ml (a slight excess) of 10% sodium hydroxide; 35 g (excess) of 40% formaldehyde solution are added, and the whole allowed to remain at room temperature for 6 days. Then it is neutralized with hydrochloric acid, extracted repeatedly with ether, and the latter removed on a water bath. If necessary, the residue is steam distilled to remove unchange phenol, and the obtained mixture of ortho and para benzyl alcohols is shaken with cold benzene until nothing further dissolves. The ortho compound, which is much the more soluble, is thus separated from the para-isomer. Yield including both compods, 80% theoretical (32 g). o-Hydroxybenzyl alcohol (saligen) forms colorless crystals; m.p 82° C; the p-hydroxybenzyl alcohol (4-hydroxybenzyl alcohol) melts at 112° C.

Systematic organic chemistry, by W. M. Cumming, 72, 1937.

IUPAC Name

4-(hydroxymethyl)phenol

InChI

InChI=1S/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H2

InChI Key

BVJSUAQZOZWCKN-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1CO)O

MeSH Synonyms

4-(Hydroxymethyl)phenol, 4-hydroxybenzyl alcohol, 4-methylol phenol, gastrodigenin, p-hydroxybenzyl alcohol

Depositor-Supplied Synonyms

4-hydroxybenzyl alcohol, 4-(Hydroxymethyl)phenol, 623-05-2, p-Hydroxybenzyl alcohol, p-Methylolphenol, 4-Methylolphenol, 4-Hydroxybenzenemethanol, p-(Hydroxymethyl)phenol, Benzenemethanol, 4-hydroxy-, Gastrodigenin, 4-Hydroxybenzylalcohol, alpha-Hydroxy-p-cresol, Benzyl alcohol, p-hydroxy-, 4-Hydroxymethyl-phenol, Parahydroxybenzyl Alcohol, a-hydroxy-p-cresol, p-hydroxy-Benzyl alcohol, B4-hydroxy-enzenemethanol, .alpha.-Hydroxy-p-cresol, CCRIS 5114, CHEMBL202132, CHEBI:67410, BVJSUAQZOZWCKN-UHFFFAOYSA-N, Benzyl alcohol, p-hydroxy- (8CI), EINECS 210-768-0, Benzenemethanol, 4-hydroxy- (9CI), SBB059322, NSC 227926, 4-(hydroxymethyl)phenol (ACD/Name 4.0), 4-hydroxymethylphenol, 4-hydroxymethyl phenol, 4-hydroxybenzyl-alcohol, 4-Hydroxy-benzylalcohol, 4-Hydroxyphenyl methanol, 4-Hydroxyphenyl Carbinol, 4-hydroxy benzyl alcohol, 4-hydroxy-benzyl alcohol, 4HBA, para-hydroxybenzyl alcohol, 4-hydroxyl-benzyl alcohol, (4-Hydroxyphenyl)methanol, ACMC-1BDK0, bmse000623, bmse010028, UNII-1A3AH1FP1B, AC1Q7C0X, AC1Q7C8A, 1A3AH1FP1B, SCHEMBL62690, H20806_ALDRICH, KSC489M6F, ARONIS24225, W398705_ALDRICH, (4-hydroxyphenyl)methan-1-ol, HYDROXYBENZYL-4 ALCOHOL, AC1L18J9, PARAGOS 420603, RARECHEM AL BD 0098, 54860_FLUKA, CTK3I9662, FEMA 3987, HMDB11724, MolPort-000-139-973, ZINC388762, ACT01155, STR00674, ANW-34146, AR-1F7058, BBL025863, BDBM50177408, NSC227926, STL284640, ZINC00388762, AKOS000121529, AS00576, MCULE-8377025602, NSC-227926, PS-3494, RP19568, RTC-063801, 4CN-0695, AC-10981, AJ-20768, AK-47325, AN-16391, BC227836, BR-47325, CJ-03341, KB-39158, LS-30758, OR010965, OR189822, OR304873, SC-18384, TL806254, ZB011693, AB0010766, DB-003490, KB-192719, ST2418404, TC-063801, AM20050567, FT-0618701, ST45053891, A15709, C17467, 3B4-1138, I01-0336, Q-200481, InChI=1/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H

Removed Synonyms

4-methylol phenol, p-Hydroxybenzaldehyde, CID125, 4-Hydroxybenzoic acid sodium salt, H0224, M-3990, C018966, 6329-31-3, HBA

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