Benzoic acid, 4-[(methylsulfonyl)oxy]-, methyl ester → Methanesulfonic acid 4-hydroxymethyl-phenyl ester

HRID 709464Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen atmosphere 4-methanesulfonyloxy-benzoic acid methyl ester (2.3 g, 10 mmol) was dissolved in dry THF (50 mL) and LiAlH4 (0.28 g, 10 mmol) was added at 0° C. After the addition was completed the ice bath was removed and stirring was continued at r.t. for 2 h. The mixture was cooled down to 0° C. again and excess LiAlH4 was hydrolyzed by the addition of MeOH, H2O and aq. HCl (2N). After extracting DCM the combined organic layers were dried (MgSO4) and evaporated under reduced pressure to afford the crude but mainly pure product as an oil which was used in the next step without further purification (1.95 g, 96.4%). 1H NMR (400 MHz, CDCl3): δ 7.35-7.37 (d, 2H), 7.21-7.23 (d, 2H), 4.65 (s, 2H), 3.09 (s, 3H).

Workup

additionAfter the addition
customwas removed
additionexcess LiAlH4 was hydrolyzed by the addition of MeOH, H2O and aq. HCl (2N)
extractionAfter extracting DCM the combined organic layers
dry with materialwere dried (MgSO4)
customevaporated under reduced pressure
customto afford the crude but mainly pure product as an oil which
customwas used in the next step without further purification (1.95 g, 96.4%)

Sources & evidence

ORD record: ord-e506cfd888fd4230a3f64979e027940d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181181B2

Reaction notes

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